37+ Luxury Vacation Rentals & Cabins in Winnetka |
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Winnetka Cabin Rentals

About Winnetka Vacation Rentals

There are more than 37 incredible getaway rentals that are available in Winnetka. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Winnetka.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Winnetka, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Winnetka. Places to stay near Winnetka are 916.17 ft² on average, with prices averaging US $344 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Winnetka. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Winnetka

Type Count
Vacation Homes 22
Holiday Apartments 2
Villas 2

Use these Quick Filters to Find a Vacation Rental in Winnetka

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Winnetka with Cabinns.com.

Weather in Winnetka, IL

View the weather forecast for Winnetka before booking your Winnetka Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Winnetka Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Winnetka. Discover Top Attractions For Your Next Outdoor Adventure.


Chocolate Box
Maple Street Beach
Elder Lane Beach
Home Alone House
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Brookfield Zoo

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Chocolate Box 273 Properties
Home Alone House 255 Properties
Maple Street Beach 251 Properties
Northfield 59 Properties
Elder Lane Beach 48 Properties
New Trier 30 Properties

Frequently Asked Questions About Winnetka?

What are the top cabins, lake houses & summer homes in Winnetka?

We provide an array of great vacation destinations in Winnetka. If you are looking to stay in or around the Winnetka area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winnetka:

Which cabin rental, resort, or holiday home in Winnetka is best for families?

Searching for a family-friendly cabin in Winnetka? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Winnetka?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 37 in the Winnetka area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Winnetka.


People Also Ask

There are 10 hotels in Winnetka and 26 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Winnetka